213306
苯基乙烯基亚砜
95%
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线性分子式:
C6H5SOCH=CH2
化学文摘社编号:
分子量:
152.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
243-831-6
Beilstein/REAXYS Number:
2039218
MDL number:
产品名称
苯基乙烯基亚砜, 95%
InChI key
MZMJHXFYLRTLQX-UHFFFAOYSA-N
InChI
1S/C8H8OS/c1-2-10(9)8-6-4-3-5-7-8/h2-7H,1H2
SMILES string
C=CS(=O)c1ccccc1
assay
95%
form
liquid
refractive index
n20/D 1.585 (lit.)
bp
93-95 °C/0.2 mmHg (lit.)
density
1.139 g/mL at 25 °C (lit.)
functional group
sulfoxide
storage temp.
2-8°C
Quality Level
Gene Information
human ... LOC129293(129293)
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General description
Phenyl vinyl sulfoxide reacts with lithium enolates of ketones at -78°C in THF to yield bicyclo[n.2.0]alkan-1-ols. It also reacts with in situ generated (dialkylamino)magnesium reagent to yield symmetrical β-(dialkylamino)dithioacetals. It participates as an acetylene equivalent in Diels-Alder reactions.
存储类别
10 - Combustible liquids
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
X Ji et al.
Acta crystallographica. Section B, Structural science, 45 ( Pt 1), 93-99 (1989-02-01)
Three diastereomers of bicyclo[2.2.1]hept-5-en-2-yl phenyl sulfoxide were prepared by Diels-Alder [4 + 2] cycloadditions between phenyl vinyl sulfoxide and cyclopentadiene. The isomers were separated by column chromatography on silica gel and repeated recrystallizations gave the pure racemates of three of
Use of phenyl vinyl sulfoxide as an acetylene equivalent in Diels-Alder cycloadditions.
Paquette LA, et al.
Journal of the American Chemical Society, 100(5), 1597-1599 (1978)
Masataka Kawakita et al.
The Journal of organic chemistry, 62(23), 8015-8017 (2001-10-24)
Vinyl sulfoxides (PhSOCR(1)=CHR(2): R(1) = H, Me, or Ph; R(2) = H or Me) were treated with (dialkylamino)magnesium reagents, generated in situ from the reaction of EtMgBr with secondary amines (R(3)R(4)NH: R(3) = Et, i-Pr, or Bn; R(4) = Me
Wendy A Loughlin et al.
Organic & biomolecular chemistry, 1(8), 1347-1353 (2003-08-22)
The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 degrees C in THF react with (+/-)-phenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel
商品
The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.
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